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So it goes like this:

“Sally, you look groovy. You aim to win at the best DRESS competition tonight, don’t you?”
"Sally, you look groovy. You aim to win at the best DRESSED competition tonight, don’t you?”

I've heard people say best dress cannot be used in the context of boys because they do not wear "dresses". But what if the context if a girl? Is one sentence more grammatically correct than another?

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  • Servicemen were a dress uniform and boys/men can wear dress shirts. – Andrew Leach Sep 30 '13 at 14:32
  • Yeah, but that's not the main point. – CreativeWriting Sep 30 '13 at 14:37
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The competition you speak of is called "Best Dressed," not "Best Dress." Your first example is therefore incorrect. The second one is fine.

Now, there could be, in theory, a "Best Dress" competition if, for example, a bunch of seamstresses compete in making the best dress, with judges determining which dress of the ones submitted for judging is the best dress of all.

Then, too, you could re-word sentence number one as follows, but doing so would change its meaning completely. (I've added more sentences to make my meaning clear.)

"Sally, you look groovy. By the way, I hope you win the best-dress competition tonight, but the competition will be fierce. I hear that over 60 seamstresses submitted dresses to be judged. Good luck!"

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I think the grammar of both sentences is correct.

In the first sentence you are talking about the dress itself and maybe the person wearing it doesn't matter.

In the second one you are talking about the person who is dressed better.

I think, therefore, it's a matter of context and meaning, not grammar.

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